Straight Male / 40
I Want To Fuck My Old Boss
Back in college, I was an RA, my first job. My boss, Lisa, was a total bitch - she was in her 30s and from some of her comments it was clear that she was a failed counselor and was doing the job of hall director as a stop-gap until better else came along. She used to go out once a week and come back to the building drunk - all the staff knew not to bother her on Wednesday nights. She was the kind of boss that you just couldn't make happy, even when you made the mark she made you feel like you didn't. I really hated working for her at that time.
Fast forward to about five years ago, and our paths crossed again. Now in her 50s, she was a counselor, had sobered up (she did have a drinking problem), and had undergone a transformation. She was happy. We became friends on social media, and you could see a HUGE difference.
And that's when it started, my curiosity about if she was satisfied in ALL aspects of her life. She's not hot by any means - she has crow's feet that hit when she smiles (which is often) and bright blue eyes, honey blonde hair that sits shoulder length. I like her cute glasses she wears, classic but sassy. Decent use of skincare products and makeup. She's skinny but thick, with a generous backside and thighs, not much in the way of tits at all. But there is something attractive about her now, her energy and genuine happiness make her appealing.
I want to fuck her - see if I could please her, see that pussy (which I'm sure is shaved), and cum all over her decently flat stomach at least if not inside her. It's been 20 years, I think I know enough now to help her get the job done.
Fast forward to about five years ago, and our paths crossed again. Now in her 50s, she was a counselor, had sobered up (she did have a drinking problem), and had undergone a transformation. She was happy. We became friends on social media, and you could see a HUGE difference.
And that's when it started, my curiosity about if she was satisfied in ALL aspects of her life. She's not hot by any means - she has crow's feet that hit when she smiles (which is often) and bright blue eyes, honey blonde hair that sits shoulder length. I like her cute glasses she wears, classic but sassy. Decent use of skincare products and makeup. She's skinny but thick, with a generous backside and thighs, not much in the way of tits at all. But there is something attractive about her now, her energy and genuine happiness make her appealing.
I want to fuck her - see if I could please her, see that pussy (which I'm sure is shaved), and cum all over her decently flat stomach at least if not inside her. It's been 20 years, I think I know enough now to help her get the job done.
